System Administrator, Boston

At WHOOP, we're on a mission to unlock human performance. WHOOP empowers members to perform at a higher level through a deeper understanding of their bodies and daily lives.
WHOOP is building a deeply technical IT organization and is looking to add System Administrators. Good fit candidates will be technical folks earlier on their growth path towards Engineer roles.
These roles are responsible for execution. Leadership and senior engineers are setting our roadmap, and our SysAdmins will deliver against that roadmap. You will work on projects to improve employee experience, identity & access management, automation & self-service, endpoint engineering, corporate security, event production & AV, compliance readiness, and more. As an early member of a small but fast-growing team, candidates must be ready and excited to take on significant responsibility and do whatever is needed to help the team be successful. Some days that will involve deep work on long term projects. Other days that will involve responding to urgent problems that popped up unexpectedly.
This role will collaborate closely with company leadership, Security functions, Risk & Compliance, IT Support, Business Systems, and more.
These roles will get exposure to all parts of our IT environment, and we have a mountain of work to accomplish. We don’t expect superhuman results from one individual - but we do want to attract someone who is motivated by the challenge, energized to solve technical problems, and wants to get a lot of repetitions on interesting projects.
Responsibilities

Configure systems, implement new features, and troubleshoot issues across our IT environment
Provide expert management of third-party applications we rely on
Harden our corporate security posture
Execute against an IT roadmap and deliver results
Eliminate root causes of IT support tickets and manual IT work through automation and process engineering
Build automation and self-service capabilities to remove employee friction and enhance corporate efficiency
Contribute meaningfully in helping us build AI-first IT operations; our aspirations stretch far beyond HelpDesk automation
Develop monitoring, observability, and reporting capabilities
Identify and mitigate IT risks to business continuity
Communicate proactively and clearly with employees and business partners, ensuring alignment and transparency around our plans and the trade-offs we’re making
Assist our IT Support team with escalations, coaching, and mentorship
Qualifications

Proven experience working on innovative systems and processes from the ground up
Programming skills to enable automation and custom solutions
Hands-on administration experience with cloud infrastructure (AWS/GCP)
Strong knowledge of Mac & Windows operating systems, identity management, and corporate security best practices
Experience managing large fleets of corporate computing devices
Experience working on large-scale implementations and/or migrations of critical IT systems
Experience working on AI projects, ideally driving broad usage and impact in the workplace
Excellent communication skills, with the ability to explain technical concepts to non-technical audiences
Strong judgment in prioritization and solution design, balancing impact and maintenance costs
Ability to work independently and take initiative in a rapidly changing environment
A demonstrated employee-first mindset, actively listening and engaging with users and making their lives better
This role is based in the WHOOP office located in Boston, MA. The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office.
Interested in the role, but don’t meet every qualification? We encourage you to still apply! At WHOOP, we believe there is much more to a candidate than what is written on paper, and we value character as much as experience. As we continue to build a diverse and inclusive environment, we encourage anyone who is interested in this role to apply.
WHOOP is an Equal Opportunity Employer and participates in E-verify to determine employment eligibility
The WHOOP compensation philosophy is designed to attract, motivate, and retain exceptional talent by offering competitive base salaries, meaningful equity, and consistent pay practices that reflect our mission and core values.
At WHOOP, we view total compensation as the combination of base salary, equity, and benefits, with equity serving as a key differentiator that aligns our employees with the long-term success of the company and allows every member of our corporate team to own part of WHOOP and share in the company’s long-term growth and success.
The U.S. base salary range for this full-time position is $75,000 - $120,000. Salary ranges are determined by role, level, and location. Within each range, individual pay is based on factors such as job-related skills, experience, performance, and relevant education or training.
In addition to the base salary, the successful candidate will also receive benefits and a generous equity package.
These ranges may be modified in the future to reflect evolving market conditions and organizational needs. While most offers will typically fall toward the starting point of the range, total compensation will depend on the candidate’s specific qualifications, expertise, and alignment with the role’s requirements.